For the most heralded classic menswear brands in the world, heritage is a home run. When you can boast century-plus commitment to your craft, you work does the talking for you. Italy is rightfully the home to many of menswear’s greatest operations and among them is Isaia.

Founded initially in 1920, Isaia is one of many classical tailoring companies that call Naples home. In its original form, it was not a label as we think of it now, but a family business that began as a fabric store for the city’s best tailors, founded by Enrico Isaia. Enrico, of course, was a tailor himself who—according to current CEO and great grandson Gianluca—learned the art of tailoring from Cesare Attolini, the son of Vincenzo Attolini, the renown Italian tailor who created the famous neapolitan suit jacket (more on that later).

Eventually, that fabric store grew to encompass a workshop next door that became a bespoke, custom-made store for Naples’ tailors to work out of. Years later, in 1957, the company was truly founded. Enrico enlisted his brothers Rosario and Corrado to move the company to a nearby village, Casalnuovo, where Isaia remains to this day. At the time, roughly 14,000 people lived there and an astounding 7,000 of them were tailors—according to Gianluca. Among this rich population of classically trained tailors, Isaia was primed to become a true tailoring brand.

Originally, that meant producing suits for some of fashion’s big names. But the following decades saw the company expand rapidly, before finally exporting the brand’s collection in the late ‘80s and making the Isaia name truly worldwide. To this day, it remains a family-run enterprise. CEO Gianluca Isaia and his family members represent the third generation of family ownership, controlling the overall brand strategy and marketing while his sister and cousins handle the product, operations and administrations aspects of the business.

Closing in on the 100th anniversary of the original Isaia operation and celebrating the 60th anniversary of suiting operation this year, the company has not just clearly established itself in the lexicon of well-informed menswear watchers, but also remained relevant for fashion’s foremost. While Isaia may not be responsible for the most bombastic runway shows each season or intent on trying new trends every few months, Isaia has figured out the careful balance of old world neapolitan tailoring roots and covetable pieces made for the current day. Much of that can be credited to the brand’s twisting of its neapolitan style at its core. It’s ability to occupy that middle ground may be its most formidable skill—it may not hang with the Kitons, Attolinis or Rubinaccis in terms of pure suiting prowess, but Isaia’s ability to infuse this storied style with modern materials, details and flair puts it in a category all its own.

Tracing the history and heritage of a suiting brand like Isaia can be tricky. They often remain under the radar as enterprises, churning away and creating quality product far outside the spotlight. Unlike the mainstream, often multinational consumer corporations that populate the runway each season, Italian suit makers like Isaia and its compatriots tend to shy away from the seasonal calendars and trends. After all, their offering has held a steady place in mens’ closets for decades and withstood the cycles of styles fading in and out of their wardrobes. That, along with the 1-of-1 bespoke nature that defines custom suiting and the “off the rack” shopping philosophy of shoppers who simply need serviceable suiting tend to keep brands like Isaia isolated from the “fashion” spectrum.

Image from the Fall/Winter 2017 lookbook

Still, the inherent rebelliousness of Isaia is its defining characteristic. The company describes its man as offbeat and provocative—not necessarily one to care about the rules, let alone follow them. This comes through incredibly clear in the brand’s penchant for outlandish patterns and color palettes, as well as sharp lines and silhouettes that define neapolitan tailoring.

While the technical definition of neapolitan was created by Vincenzo Attolini when he removed the extra padding and lining from a British suit jacket to keep wearers cool in the balmy Italian climate, one could argue that the brand that best embodies the modern neapolitan aesthetic is Isaia. With its wide peak lapels, love of windowpane patterns and color combinations that most other classic brands wouldn’t touch, Isaia has created its own definition for neapolitan style. Gianluca himself is a practitioner as he is unafraid to wear sandals with his most formal of suits. This essence of sprezzatura comes through in many of Isaia’s designs, whether it’s the functional surgeon’s cuffs buttons on the sportcoats or the efforts to bring more modern materials into an age old practice. This includes innovations like Aquacashmere—delicate cashmere that undergoes Isaia’s “Aqua treatement”—leaving the item stain and water-resistant. You haven’t seen the IDGAF nature of Italian suiting until you’ve spotted a man wearing a blazing orange, windowpane sport jacket and thought, “I could wear that too.”

Isaia CEO Gianluca Isaia

But even with a brash sense of style that lends itself well to Pitti peacocks and sprezzatura devotees, Isaia is hardly one to skimp on the details. It may be open to the aesthetically brash, but these small touches help the label stand apart. As Isaia outlines, unique tailoring details include: slanted breast pockets (reminiscent of Neapolitan fishing boats) on all Isaia jackets, extra fabric on the front under-collar (a nod to the needs for frugal, post-war Italians), small, high-set Neapolitan arm holes, hand-stitched buttonholes edged in glossy silk and waistbands in breathable Sea Island cotton are just a selection of the time intensive touches that accentuate Isaia's offerings year after year. Naturally, no Isaia garment is complete with a several rounds of stringent ironing, pressing (all by hand, of course).

Clearly the brand invests an immense amount of time doing things the "right" way, but its the label's ability to embody a relaxed, intuitive Italian ease that makes it consistently one of the best labels in menswear.

Part of that nonchalance is fueled by Isaia’s best known symbol: the red coral that pops up on the lapel of its suits. But it’s more than a brand signifier. The red coral of Naples is believed to have sprung from mythical origins, and is a key symbol in Neapolitan culture. The Greek hero Perseus, returning home to deliver the head of Medusa to his soon-to-be stepfather, made a pitstop to save the beautiful Andromeda from divine judgment. During the rescue, he set down the head of Medusa, leaving her blood to drip into the sea—resulting in the creation of red coral. As a symbol, it embodies good luck—not just for a brand like Isaia—but to all of Naples. As such, the area has become a hotbed of coral used for everything from jewelry to religious ornaments.

While Isaia’s aesthetic could put off fans of more inconspicuous styles made for the likes of an accountant or financial advisor, Isaia plays a bit more broadly as Gianluca Isaia describes. “We have customers that are looking for classic design but with more style and customers looking for a lot of style but also quality. They want to look fresher, younger, sexier. So we are right in the middle.”

Normally, that middle ground would spell doom for a mainstream brand—one unwilling to take risks on divisive pieces or unable to create reliable everyday staples. But for a classical menswear brand like Isaia, being in the middle might be its greatest strength.